Never Good Enough
by Apocalyptic-Mess
Summary: As Sam continued on with his stories, his descriptions of Dean, the perfect brother, the perfect person, she knew. It didn't take long for Jessica to figure out that in Sam's eyes, she would never be good enough. Sam/Jess


**Never Good Enough**

Jessica Moore didn't know that Sam Winchester had a brother; he'd made sure of that.

All that Jess knew about Sam's family was that his mother had died when he was little and he'd had a falling out with his father shortly before leaving for Stanford. Sam never mentioned Dean, even though Jess knew he was hiding _something_.

There were never any pressuring questions, no probing queries. Jess had only ever asked once about Sam's family, and his mom and dad's names were all he'd given up. Any siblings? she'd asked, but Sam had never confirmed or denied. He'd caught Jess on the phone once, talking about him with Nick, one of Sam's best friends. She'd been asking Nick about Sam's family, and he'd had silently cursed himself. Nick knew that Sam had a brother that he'd mentioned in passing, but as far as he could remember, his friend knew nothing else about the Winchesters messed up family.

Then, when Jess had hung up the phone and while Sam was too shocked that Jessica would _care_ enough about him to try and dig into his life, she turned around and noticed him. Sam stood there, watching her, waiting for her to say something along the lines of "you lied to me", or "why didn't you tell me you had a brother?".

While Jess was waiting for Sam to say something to her, Sam's mind was blank. When Sam said nothing, Jess at least had the decency to look ashamed. She waved the phone in her hand, mumbling nervously, "Just . . . Nick said . . ." but she couldn't finish the thought. Sam, having no idea _what_ Nick had said, only nodded.

Apparently, Jess took that as confirmation of the story which Nick had fed her, which was that Sam _had_ had a brother, but he'd died, probably in the house fire that had killed Sam's mom; which was why Sam failed to mention his family almost ever.

Jess just thought Sam had a dead brother. Sam knew she wouldn't have understood the real reasons.

As far as Sam was concerned, Dean was _his_ secret, his personal hero, and Sam didn't want to share him with the rest of humanity.

Sam never really got over his hero worship of his big brother. Dean would always be his idol, the one who had taken care of him after their mom had died and their dad had gone on a suicide/revenge mission. Would Jess have understood that? That Sam needed something just to himself because he was so used to having nothing at all.

Unfair as it was, Sam knew that Jess definitely would not have understood. She'd grown up in a normal family, with a normal life, normal aspirations and a normal, rational fear of the supernatural. Sam, obviously, had grown up in a very abnormal family, with a fucked-up life, _surprisingly_ normal future aspirations and the assumption that he would follow in the family business of 'taking care' of everything supernatural.

To Jessica, law school seemed pretty normal. To Dean, law school meant betraying family.

The weird thing was, Sam could rationalize with both their opinions.

But Dean was his big brother, _his_. No one else could say they had a brother like that, someone who would die for them, who had looked after them since they were six months old. No one else could say that Dean was their brother.

And Sam wanted to keep it that way.

***SPN***

Sam never told Jess about Dean, never told her about hunting. Sure, he wanted to keep her safe, wanted to move on with his life, get married, have a family. He wanted a picket fence, apple pie life, as Dean would say. But Sam couldn't deny that he wanted to hide his past. He wasn't ashamed, he never could have been, but hunting was their family business.

Family.

When Sam had dreams of marrying Jessica, Dean was still separate from these illusions. A double-life. It took him almost two years of dating Jess before he could even grasp the concept that if he was going to marry Jess, that would make her family.

Sooner or later, he'd have to tell her that his brother was alive and kicking. (Well, for the most part anyway.)

It was a normal weeknight in late November, midnight study sessions for exams which they would inevitably pass anyway, and Sam and Jess realized their neglected hungry too late to take advantage of any of the on campus facilities, and so they were running through the snow at three o' clock in the morning, to the nearest Burger Barn. They were laughing as they pushed open the doors, frozen through to the bone. Sam laughed as Jess shook her hair but the snow stuck to her like a magnet, so Sam gently brushed the snow from her shoulders, hair, her cheeks. The look in Jessica's eyes was indescribable, so full of tender, gentle appreciation that Sam had to look away, had to forget the way her personality reminded him of Dean.

So he'd cleared his throat to take attention away from their contact and his obvious discomfort, and had asked what Jess wanted to eat. Proudly, Jessica declared that she wanted the biggest, greasiest, most bad-for-you bacon cheeseburger that they had. Sam couldn't help but smile proudly at the thought, once again contrasting the similarities between this girl and his brother.

"And now, what is your wish?" Jess announced boldly, gesturing to the menu board that Sam stared at in general disinterest. Internally though, his mind was waging war. _We shouldn't have come here_. Sam had too many memories. Too many involving Dean.

Sam couldn't have a cheeseburger; they reminded him of Dean. Nor could he choose to have anything coated in grease, ketchup, and salt that could possibly lead to congestion of heart vessels and cause _any_one to have a heart attack—that, again, was just too _Dean_.

So Sam played it safe, opting for a low-fat, low-calorie salad. Jess stared at him.

"A salad, Sammy? Seriously?" Her amused chuckle was all but lost on Sam as he blinked distantly, simply giving a nod of his head.

"Lame."

Jessica's hushed declaration pulled at every single one of Sam's emotional heartstrings.

"_Lame." Dean announced loudly, not taking into consideration ten year old little Sammy's feelings. _

_They were buying their own supper again for the sixth night of a two week stretch that their father was gone, and Sammy had decided to get a salad instead of his regular double bacon deluxe cheeseburger—because that's what Dean always got, and Sammy wanted to be just like his big brother._

_Little Sammy refused to tell Dean why the sudden change in appetite, but in his head it was all he could think about. Sure, Sammy was a chubby kid, not having lost all of his baby fat yet, but never before had anyone at school made fun of him for it. He was going to go to his very first school dance this weekend, and he'd asked Krysta Collins if she wanted to go with him—because wasn't that what they did in the movies? If there was a dance, you asked a girl you liked if she wanted to go with you, and she always said yes._

_Apparently, Krysta Collins never got that memo, and she'd blatantly refused Sammy's offer, criticizing not only his weight, but the fact that he had a freaky, messed up family. _

_Sammy had never thought of his family as abnormal, let alone "messed up". Dean had always said they were a normal family and Sammy was almost mad at Dean for lying to him. _

_It wasn't until later as little Sammy stared at his salad that Dean had the inclination to ask what was wrong. As Sammy recounted his tale, failing to mention the point where he was just about in tears from Krysta's comments, Dean listened avidly, laughing in all the wrong places, pointing out Sammy's insecurities—Sammy never stopped, knowing that this was just _Dean_. He would never truly laugh at Sammy, never ignore if something, or some_one_ was hurting his little brother; it was just too Dean. _

_At the end of little Sammy's story, Dean cut his own burger in half and then gave half to his little bro. As soon as Dean was sure Sammy's worries were put to rest, he started up talking about hunting, and how Dad had called earlier and he would be home a few days sooner. Dean quizzed little Sammy on hunting techniques, and when Sammy got them right, Dean gave him a pat on the head and promised to take him out shooting later that week._

_All Sammy Winchester could think with pride was, _no one else has a brother like Dean.

_And little Sammy wanted to keep it that way._

Laughing softly to himself, something in Sam's head started to click and then it was like all of a sudden, there was a whole puzzle created in Sam's mind. Sam loved Dean because he was his brother. Sam loved Jess because she reminded him of Dean, but a Dean who didn't have to worry about hunting, one who didn't have to leave for weeks at a time. Jess was his normal life, all wrapped up with a bow. He gazed at Jessica with soft eyes, and said, "You remind me of Dean."

Jessica blinked vacantly at him, not comprehending a word of Sam's apparent random muttering. When Sam just smiled, she felt compelled to ask. "Who's Dean?"

Jess thought of a thousand different answers; a childhood friend, a dead family pet, an uncle who Sam had lost contact with. None of her assumptions were even close to right.

"He's . . ." Sam smirked contentedly and chuckled. "He's my brother."

If Jess had been drinking anything, she would have choked on it and coughed all over Sam; as it was, somehow she managed to choke on her own spit, disgusting as it was.

"Your br-brother?" She coughed out unsuccessfully as Sam stared at her, trying to gage the threshold of her reaction. Other than the obvious shock, something in her eyes caused Sam to tilt his head in confusion.

Disbelief. The kind that questioned Sam's sanity.

"Yes." Sam stated calmly because Jess was staring at him like he'd turned into a unicorn and she couldn't tell whether to be fascinated or back away. He didn't like the thought of her backing away from him so he carefully took her hand. "Yes," Sam repeated. "My brother."

Twenty minutes later, Sam would still be able to feel the sting from her hand connecting with his face. They'd been asked to leave promptly following their apparent relationship abuse. They made their way to a deserted park, selecting a particularly secluded wooden bench. Jess made sure to keep at least half a foot of space between them as she demanded Sam to explain.

So Sam did. He told Jess that Dean was his big brother, older by four years. Apparently, Dean and Jess even shared the same birthday. January 24th. Sam told Jess that Dean had practically raised him after their mother had died, and that Dean loved pie and Led Zeppelin and cheeseburgers. His least favourite holiday was Halloween (except for the candy) but he loved Valentine's Day, for reasons better known only to Dean.

Sam could have told her everything. He'd spent his whole life watching Dean, trying to be just like his big brother (excluding Dean's choice in music), trying his hardest to make his brother proud. He'd gotten into Stanford just to make his brother proud.

The longer Sam talked, the more apparent it became: No one would ever be able to compete with Dean. Sam loved her, sure. Loved her enough to want to marry her? That was debatable, but Jess loved Sam, and she knew he loved her too. No one could argue that, but even if Jessica tried for the rest of her life, Sam would never have that same undying faith and loyalty in her.

As Sam continued on with his stories, his descriptions of Dean, the perfect brother, the perfect person, she knew. It didn't take long for Jessica to figure out that in Sam's eyes, she would never be good enough.

If there was ever a choice between Dean and Jessica, if she was being 100% completely honest with herself, she knew who Sam would choose.

Months later, when she flicked on the light to the living room in the middle of the night and was introduced to him, she knew.

What was worse was the thought that maybe . . . maybe she'd always known.

She knew it would be their last goodbye.


End file.
